KR20110116049A - 결핵의 치료, 예방 및 관리를 위한 pde4 조절제를 포함하는 조성물 및 사용 방법 - Google Patents
결핵의 치료, 예방 및 관리를 위한 pde4 조절제를 포함하는 조성물 및 사용 방법 Download PDFInfo
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- KR20110116049A KR20110116049A KR1020117021146A KR20117021146A KR20110116049A KR 20110116049 A KR20110116049 A KR 20110116049A KR 1020117021146 A KR1020117021146 A KR 1020117021146A KR 20117021146 A KR20117021146 A KR 20117021146A KR 20110116049 A KR20110116049 A KR 20110116049A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- amino
- hydrogen
- Prior art date
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- 201000008827 tuberculosis Diseases 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 42
- 238000011282 treatment Methods 0.000 title abstract description 36
- 239000000203 mixture Substances 0.000 title description 29
- 230000002265 prevention Effects 0.000 title description 11
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 title 1
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims abstract description 115
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims abstract description 115
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 239000012453 solvate Substances 0.000 claims abstract description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 284
- -1 moxifloxin Chemical compound 0.000 claims description 275
- 125000000217 alkyl group Chemical group 0.000 claims description 211
- 150000001875 compounds Chemical class 0.000 claims description 128
- 125000003545 alkoxy group Chemical group 0.000 claims description 93
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 82
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 75
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 69
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 66
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 66
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 208000015181 infectious disease Diseases 0.000 claims description 17
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000004442 acylamino group Chemical group 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
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- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 4
- 229960003350 isoniazid Drugs 0.000 claims description 4
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical group NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 4
- QDZOBXFRIVOQBR-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-3-oxo-1h-isoindol-4-yl]cyclopropanecarboxamide Chemical group C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(=O)C4CC4)C=CC=C3C2)=O)=C1 QDZOBXFRIVOQBR-UHFFFAOYSA-N 0.000 claims description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- VCOPTHOUUNAYKQ-WBTCAYNUSA-N (3s)-3,6-diamino-n-[[(2s,5s,8e,11s,15s)-15-amino-11-[(6r)-2-amino-1,4,5,6-tetrahydropyrimidin-6-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;(3s)-3,6-diamino-n-[[(2s,5s,8 Chemical compound N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1.N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1 VCOPTHOUUNAYKQ-WBTCAYNUSA-N 0.000 claims description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
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- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 claims description 2
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- VRDIULHPQTYCLN-UHFFFAOYSA-N Prothionamide Chemical compound CCCC1=CC(C(N)=S)=CC=N1 VRDIULHPQTYCLN-UHFFFAOYSA-N 0.000 claims description 2
- 229930003270 Vitamin B Natural products 0.000 claims description 2
- ZWBTYMGEBZUQTK-PVLSIAFMSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23-dioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(32),2,4,9,19,21,24,26,30-nonaene-28,4'-piperidine]-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c4NC5(CCN(CC(C)C)CC5)N=c4c(=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C ZWBTYMGEBZUQTK-PVLSIAFMSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 2
- 229960004821 amikacin Drugs 0.000 claims description 2
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
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- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 2
- 229960002626 clarithromycin Drugs 0.000 claims description 2
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Classifications
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/4035—Isoindoles, e.g. phthalimide
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Communicable Diseases (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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US15146709P | 2009-02-10 | 2009-02-10 | |
US61/151,467 | 2009-02-10 |
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KR20110116049A true KR20110116049A (ko) | 2011-10-24 |
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KR1020117021146A KR20110116049A (ko) | 2009-02-10 | 2010-02-09 | 결핵의 치료, 예방 및 관리를 위한 pde4 조절제를 포함하는 조성물 및 사용 방법 |
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US (1) | US20120149716A1 (fr) |
EP (2) | EP2395995A1 (fr) |
JP (2) | JP2012517441A (fr) |
KR (1) | KR20110116049A (fr) |
CN (1) | CN102387798A (fr) |
AP (1) | AP3437A (fr) |
AU (1) | AU2010213936B2 (fr) |
BR (1) | BRPI1007500A2 (fr) |
CA (1) | CA2750123A1 (fr) |
CO (1) | CO6410289A2 (fr) |
CR (1) | CR20110411A (fr) |
EA (1) | EA201171035A1 (fr) |
EC (1) | ECSP11011295A (fr) |
HK (1) | HK1205681A1 (fr) |
IL (1) | IL214176A (fr) |
MX (1) | MX2011008132A (fr) |
MY (1) | MY160002A (fr) |
NI (1) | NI201100154A (fr) |
NZ (1) | NZ594193A (fr) |
PE (2) | PE20151143A1 (fr) |
SG (2) | SG173149A1 (fr) |
UA (1) | UA103791C2 (fr) |
WO (1) | WO2010093588A1 (fr) |
Families Citing this family (9)
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CA2821805A1 (fr) | 2010-12-16 | 2012-06-21 | Celgene Corporation | Formes posologiques pour des medicaments mediocrement solubles administres par voie orale a liberation controlee et leurs utilisations |
AU2012308663B2 (en) | 2011-09-14 | 2017-06-08 | Amgen (Europe) GmbH | Formulations of cyclopropanecarboxylic acid {2-[(1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide |
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JP2015164928A (ja) | 2015-09-17 |
AP3437A (en) | 2015-10-31 |
NI201100154A (es) | 2012-01-24 |
SG10201402158VA (en) | 2014-07-30 |
PE20120580A1 (es) | 2012-05-23 |
HK1205681A1 (en) | 2015-12-24 |
EA201171035A1 (ru) | 2012-02-28 |
AU2010213936B2 (en) | 2014-07-31 |
PE20151143A1 (es) | 2015-08-07 |
AP2011005849A0 (en) | 2011-08-31 |
AU2010213936A1 (en) | 2011-08-11 |
JP2012517441A (ja) | 2012-08-02 |
NZ594193A (en) | 2013-09-27 |
US20120149716A1 (en) | 2012-06-14 |
BRPI1007500A2 (pt) | 2016-02-16 |
IL214176A0 (en) | 2011-08-31 |
ECSP11011295A (es) | 2011-09-30 |
WO2010093588A1 (fr) | 2010-08-19 |
CR20110411A (es) | 2012-01-06 |
MY160002A (en) | 2017-02-15 |
CN102387798A (zh) | 2012-03-21 |
SG173149A1 (en) | 2011-08-29 |
IL214176A (en) | 2016-09-29 |
CA2750123A1 (fr) | 2010-08-19 |
UA103791C2 (uk) | 2013-11-25 |
EP2395995A1 (fr) | 2011-12-21 |
MX2011008132A (es) | 2011-09-06 |
EP2818164A1 (fr) | 2014-12-31 |
CO6410289A2 (es) | 2012-03-30 |
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